Do you have any info regarding long-term visas in the Philippines? I haven't been there yet. (but I will start re-searching) How is the safety there?
You can come as a tourist, and extend your visa up to 36 month. After that you can take a trip to Singapore, and come back to do the same again.
They have also long term stay options, but I haven't looked deeply into it myself. Honestly, Philippines isn't my favorite in Asia, but it fits into your requirements.
It's a huge place, with many islands and many different kind of people.
Security wise it's like everywhere, don't flash your money and you'll be ok. Shops and banks have a guy with a shotgun for security outside, but I guess that's not much different from Caribbean islands.
I spent 4 months there, one month on a beautiful tiny island in the middle of the ocean (no tourists there, you can walk around the island in 15 minutes), after that Boracay was a huge disappointment.
I liked the mountains north Manila the most (Sagada), lovely locals walking around the rice terraces listening to American country music on their radio, perfect English there and very peaceful. You can even find coffeeshops (the Amsterdam type) there if you keep your eyes open.
Negatives: shitty food, beggars, pod people with hive mind and crab mentality (no offense to Filipinos).
You can also check Malaysia (Georgetown, KL), Singapore, or even Bali (but all of there won't fit 100% into your requirements).
Taiwan is good taxwise, they speak English too, but the culture is very traditional Chinese and I don't know about the visa things for people without any connection to the country.